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tert-Butyl 4-formylpiperidine-1-carboxylate → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine

HRID 429824
Notes
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Reaction equation

HRID 429824 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([NH:13][CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH:29]=O)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:29][CH:26]3[CH2:27][CH2:28][N:23]([C:21]([O:20][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:22])[CH2:24][CH2:25]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 11106515(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine

Product 1

HCID 54410775(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amineYield 82%

Reagents, catalysts & solvents 1

HCID 6365
1,1-Dichloroethane
Solvent

Procedure

To a solution of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine (2.38 grams, 11.6 mmol) and 1-(tert-butoxycarbonyl)piperidine-4-carboxaldehyde (2.47 grams, 11.6 mmol) in dichloroethane (20 ml) was added sodium triacetoxyborohydride (3.67 grams,17.4 mmole). The reaction mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with water, dried over potassium carbonate and concentrated under reduced pressure to leave a residue, which was purified by flash chromatography on silica gel using 30% ethyl acetate in hexane. Appropriate fractions were combined and concentrated to give (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine as a oil (3.78 g, 82%), M+H 403.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. washThe organic layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated under reduced pressure
  6. customto leave a residue, which
  7. customwas purified by flash chromatography on silica gel using 30% ethyl acetate in hexane
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a91d7d497a014bb0ad40f5ff789587b3
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06319920B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes