Sodium Hydroxide → HCID 69491289, compound

HRID 430605Notes

Reaction equation

HRID 430605 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([CH2:24][CH:25]=O)=[CH:16]1.[NH:27]1[CH2:32][CH2:31][CH:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:29][CH2:28]1.[OH-].[Na+]>ClCCl.C(O)(=O)C>[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([CH2:24][CH2:25][N:27]2[CH2:28][CH2:29][CH:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:31][CH2:32]2)=[CH:16]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 18351319(1-Benzofuran-3-yl)acetaldehyde

Product 1

HCID 69491289HCID 69491289, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

13 ml of acetic acid and 61 g of sodium triacetoxyborohydride are added in succession to a solution of 33 g of 2-(benzofuran-3-yl)acetaldehyde and 41.3 g of tert-butyl 4-piperidylcarbamate in 1.4 litres of dichloromethane. After 24 hours' stirring at room temperature, a 20% sodium hydroxide solution is added. After 10 minutes, the reaction mixture is decanted and the organic phase is washed, dried and concentrated. Chromatography over silica gel (cyclohexane/ethyl acetate 30/70) enables the expected product to be isolated.

Workup

  1. waitAfter 10 minutes
  2. customthe reaction mixture is decanted
  3. washthe organic phase is washed
  4. customdried
  5. concentrationconcentrated
  6. customto be isolated

Sources & evidence

ORD record
ord-86f882e08c344f9aa0aabcef822b26d7
Source dataset
uspto-grants-2001_11
Patent number
US06323217B2

Reaction notes

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