Sodium borohydride → HCID 67345922, compound

HRID 1670010Notes

Reaction equation

HRID 1670010 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([C:24](=[O:33])[C:25]([CH3:32])([CH3:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])[CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[BH4-].[Na+]>C1COCC1>[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([C:24](=[O:33])[C:25]([CH3:32])([CH3:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])[CH:17]2[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67344535HCID 67344535, compound

Product 1

HCID 67345922HCID 67345922, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Step A of Intermediate 126, (3S)-1-cbz-3-[acetyloxypivaloyl (4-oxo-cyclohexyl)amino]pyrrolidine (1.60 g, 3.49 mmol) was dissolved in THF (15 mL), and NaBH4 (172 mg, 4.19 mmol) was added at rt. After being stirred for 12 h, the reaction mixture was quenched with water, and the organic material was extracted with EtOAc. The extracts were dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (EtOAc/Hex=1/1) to give the title compound (1.481 mg, 92.1%).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionthe organic material was extracted with EtOAc
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by column chomatography (EtOAc/Hex=1/1)

Sources & evidence

ORD record
ord-a491e36e6a5248fa9e982790cc717dc5
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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