Sodium borohydride → tert-Butyl 4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxopiperazine-1-carboxylate

HRID 1466062Notes

Reaction equation

HRID 1466062 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:12](=[O:28])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C:15]1=[O:27].[BH4-].[Na+]>CO>[OH:28][CH:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][C:15]1=[O:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131732683tert-Butyl 4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-oxoethyl]-3-oxopiperazine-1-carboxylate

Product 1

HCID 89526106tert-Butyl 4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-Butyl 4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-oxoethyl]-3-oxopiperazine-1-carboxylate (160 mg, 0.41 mmol) in MeOH (10 ml) was added NaBH4 (31 mg, 0.82 mmol). The reaction was allowed to stir at RT for 2 hours. TLC showed clean conversion. The reaction was quenched by addition of water. The crude material was diluted with EtOAc, washed with water, dried over sodium sulfate, and concentrated to give the title compound. LC-MS (IE, m/z): 391 [M+1]+.

Workup

  1. customThe reaction was quenched by addition of water
  2. additionThe crude material was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f05013cb1564737908bf90ff28a3b68
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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