Sodium borohydride → HCID 117966926, compound

HRID 712824Notes

Reaction equation

HRID 712824 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C@H:16]2[CH2:21][C:20](=[O:22])[CH2:19][CH2:18][N:17]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:15])[CH3:12])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>CO.O>[OH:22][CH:20]1[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:16]([C:14](=[O:15])[NH:13][C@H:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[CH3:12])[CH2:21]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 117966684HCID 117966684, compound

Product 1

HCID 117966926HCID 117966926, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To an ice cooled solution of (R)-tert-butyl 2-(((S)-1-(4-(methoxycarbonyl)phenyl)ethyl)carbamoyl)-4-oxopiperidine-1-carboxylate (D60) (300 mg, 0.75 mmol) in MeOH (25 ml) under nitrogen, NaBH4 (142 mg, 3.75 mmol) was added portionwise and the resulting mixture was stirred at RT for 18 hrs. The mixture was diluted with water (10 ml) and extracted with EtOAc (3×10 ml). The organic phases were collected, washed with NaCl sat. (20 ml) dried over Na2SO4 and evaporated in vacuo to afford the title compound (D61) (261 mg).

Workup

  1. extractionextracted with EtOAc (3×10 ml)
  2. customThe organic phases were collected
  3. washwashed with NaCl sat. (20 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-37d1c742e010422682c2d426f9d392ee
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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