tert-Butyl 4-formylpiperidine-1-carboxylate → 4-{[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 983480Notes

Reaction equation

HRID 983480 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][C:13]2[CH:12]=[C:11]([OH:15])[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6]1)[CH2:2][CH3:3].[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>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH2:25][CH:26]([CH2:29][N:4]([CH:5]2[CH2:6][CH2:7][C:8]3[C:13](=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=3)[CH2:14]2)[CH2:1][CH2:2][CH3:3])[CH2:27][CH2:28]1)=[O:22])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 100587877-Propylamino-5,6,7,8-tetrahydro-naphthalen-2-ol

Product 1

HCID 686243534-{[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 7-propylamino-5,6,7,8-tetrahydro-naphthalen-2-ol (937 mg, 4.6 mmol) and 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (1.46 g, 6.9 mmol) in dichloroethane (40 mL) was added sodium triacetoxyborohydride (2.1 g, 10.12 mmol) in a single portion. The reaction was allowed to stir at room temperature for 24 h. The reaction was concentrated in vacuo and partitioned between EtOAc (75 mL) and 5% aq. KOH (75 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford 4-{[(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (1.37 g).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between EtOAc (75 mL) and 5% aq. KOH (75 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20bb8c77ef0e4d55ac28008f80f072e8
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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