Sodium triacetoxyborohydride → tert-butyl (2S,3R)-3-hydroxy-4-(3-(2-hydroxypropan-2-yl)benzylamino)-1-phenylbutan-2-ylcarbamate

HRID 2071184Notes

Reaction equation

HRID 2071184 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH:21][C:22]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O)([CH3:24])[CH3:23].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.CCOC(C)=O>[OH:20][C@H:3]([CH2:2][NH:1][CH2:28][C:27]1[CH:30]=[CH:31][CH:32]=[C:25]([C:22]([OH:21])([CH3:23])[CH3:24])[CH:26]=1)[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamateHCID 866474433-(2-Hydroxypropan-2-yl)benzaldehyde

Product 1

HCID 59569847tert-butyl (2S,3R)-3-hydroxy-4-(3-(2-hydroxypropan-2-yl)benzylamino)-1-phenylbutan-2-ylcarbamateYield 65.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate (230 mg, 0.82 mmol) in THF was added 3-(2-hydroxypropan-2-yl)benzaldehyde (180 mg, 01.06 mmol) and stirred for 30 min at room temperature, NaB(OAc)3H (302.5 mg, 1.43 mmol) was then added portionwise in 30 min, and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with EtOAc, and washed with saturated aqueous NaHCO3. The organic layer was separated and dried (Na2SO4). Concentration in vacuo, followed purification with flash chromatography to give the desired product as a white solid (230 mg, 65% yield). 1H NMR (CDCl3): d: 8.514 (m, 2H), 7.717 (s, 1H), 7.321-7.203 (m, 5H), 3.831 (s, 3H), 3.580 (m, 1H), 2.978 (m, 1H), 2.890-2.755 (m, 3H), 1.724 (d, J=11.1 Hz, 6H), 1.364 (s, 9H).

Workup

  1. stirringthe resulting mixture was stirred at the same temperature overnight
  2. washwashed with saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration in vacuo
  6. custompurification with flash chromatography

Sources & evidence

ORD record
ord-e1f571036896470381c1ed9aa15feaec
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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