Sodium borohydride → HCID 59342433, compound

HRID 349167Notes

Reaction equation

HRID 349167 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Cl:18])[C:15](=[O:17])[CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Cl:18])[CH:15]([OH:17])[CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 588040904-(1-Chloro-2-oxo-propylidene)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59342433HCID 59342433, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 55 (1.24 g, 4.53 mmol) in ethanol (25 mL) was treated with sodium borohydride (102 mg, 2.72 mmol) at 25° C. After 1 h, the reaction mixture was concentrated in vacuo, diluted with ethyl acetate (40 mL), carefully treated with 5% aqueous hydrochloric acid (1×25 mL), the layers separated, and dried (MgSO4). The resulting solution was concentrated in vacuo to afford 56 (902.1 mg, 72%) as a colorless residue that was used without further purification. MS 298 (M+Na).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate (40 mL)
  3. additioncarefully treated with 5% aqueous hydrochloric acid (1×25 mL)
  4. customthe layers separated
  5. dry with materialdried (MgSO4)
  6. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-151469685d2d439aa7c647018ce416b0
Source dataset
uspto-grants-2007_02
Patent number
US07179805B2

Reaction notes

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