Benzaldehyde → (S)-tert-Butyl (1-benzylpiperidin-3-yl)carbamate

HRID 919598Notes

Reaction equation

HRID 919598 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>C(Cl)Cl>[CH2:15]([N:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10541535(S)-tert-Butyl (1-benzylpiperidin-3-yl)carbamateYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tert-butyl piperidin-3-ylcarbamate (2.0 g, 10.0 mmol) and benzaldehyde (1.3 g, 12.0 mmol) in CH2Cl2 under nitrogen was added NaBH(OAc)3 (4.2 g, 20.0 mmol) and the reaction was stirred for overnight. The mixture was diluted with CH2Cl2 (50 mL) and ice cooled water (20 mL). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined CH2Cl2 layer was dried over Na2SO4 and evaporated in vacuo to give the crude product which was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to afford (1.0 g, 34%) of the titled intermediate. LC-MS: m/z [M+1]=291.

Workup

  1. customThe CH2Cl2 layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined CH2Cl2 layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto give the crude product which
  6. customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Sources & evidence

ORD record
ord-4c643bbe3b5445c4a26abe22e8fc8830
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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