Sodium triacetoxyborohydride → HCID 21022369, compound

HRID 1794612Notes

Reaction equation

HRID 1794612 reaction equation
[NH2:1][CH:2]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7](=[O:15])[C:8]2[C:13]([CH3:14])=[N:12][S:11][C:9]=2[N:10]=1)[CH2:3][CH3:4].[C:23]([O:27][C:28](=[O:36])[NH:29][C:30]([CH3:35])([CH3:34])[CH2:31][CH:32]=O)([CH3:26])([CH3:25])[CH3:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[C:23]([O:27][C:28](=[O:36])[NH:29][C:30]([CH3:35])([CH3:34])[CH2:31][CH2:32][NH:1][CH:2]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7](=[O:15])[C:8]2[C:13]([CH3:14])=[N:12][S:11][C:9]=2[N:10]=1)[CH2:3][CH3:4])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamateHCID 22222280HCID 22222280, compound

Product 1

HCID 21022369HCID 21022369, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 36 (136 mg, 0.433 mmol) in MeOH (5 ml) was added (1,1-dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester(105 mg, 0.522 mmol) followed by NaBH(OAc)3 (138 mg, 0.65 mmol). The reaction mixture was stirred at room temperature overnight, quenched with water. Solvent was removed in vacuo, the residue was purified by preparative HPLC to give 37 (86 mg) at the yield of 41% for the two steps. 1H-NMR (500 MHz, CDCl3): δ 7.23–7.39 (m, 5H), 5.89 (d, J=16.0 Hz, 1H), 5.01 (d, J=16.0 Hz, 1H), 4.66 (t, J=5.77 Hz, 1H), 4.43 (brs, 1H), 2.86 (s, 3H), 2.45 (m, 2H), 2.11 (m, 1H), 1.96 (m, 2H), 1.74 (m, 1H), 1.30 (s, 9H), 1.13 (s, 3H), 1.01 (s, 3H), 0.88 (t, J=7.42 Hz, 3H).

Workup

  1. customquenched with water
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ee83a559f2d943b1b072de76d24391b3
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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