Methyl 3-formylbenzoate → HCID 59570153, compound

HRID 2071183Notes

Reaction equation

HRID 2071183 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.[CH:21]([C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([O:28][CH3:29])=[O:27])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(O)(=O)C.CCOC(C)=O>[C:15]([O:14][C:13]([NH:12][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C@H:3]([OH:20])[CH2:2][NH:1][CH2:21][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=1)[C:26]([O:28][CH3:29])=[O:27])=[O:19])([CH3:17])([CH3:16])[CH3:18]

Participants

7

Reactant 3

HCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate

Product 1

HCID 59570153HCID 59570153, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate (200 mg, 0.713 mmol) in THF was added methyl 3-formylbenzoate (117.1 mg, 0.713 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, finally 5 drops of acetic acid was added 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 (MgSO4). Concentration in vacuo was followed by purification with flash chromatography to give the desired product as a white solid (300 mg, % yield). 1H NMR (CDCl3): d: 7.999 (m, 2H), 7.589 (m, 1H), 7.451 (m, 1H), 7.254 (m, 5H), 3.956 (s, 3H), 3.892 (m, 3H), 3.549 (m, 1H), 3.040-2.850 (m, 2H), 2.793 (m, 2H), 1.374 (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 (MgSO4)
  5. concentrationConcentration in vacuo
  6. customwas followed by purification with flash chromatography

Sources & evidence

ORD record
ord-62d340f406514083a7e2c7b894dc8b09
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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