3-Methylbutanal → 2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436505Notes

Reaction equation

HRID 1436505 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:38][CH:39]([CH3:43])[CH2:40][CH:41]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:41][CH2:40][CH:39]([CH3:43])[CH3:38])[CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 115523-MethylbutanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866153742-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866153762-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dissolve (2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester (167 mg, 0.33 mmol) in 1,2-dichloroethane (2.5 mL) and add 3-methylbutyraldehyde (0.042 mL, 0.41 mmol). After 5 min, add sodium triacetoxyborohydride (100 mg, 0.47 mmol) and stir for 1 h. Add saturated aqueous sodium bicarbonate solution (5 mL) and stir for 10 min. Add ethyl acetate and separate the layers. Extract the aqueous layer with ethyl acetate, combine the organic layers, wash the organic layer with saturated aqueous sodium chloridesolution, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate) to give the title compound as a colorless oil (165 mg, 87%).

Workup

  1. customAdd ethyl acetate and separate the layers
  2. extractionExtract the aqueous layer with ethyl acetate
  3. washwash the organic layer with saturated aqueous sodium chloridesolution
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-7b15a8e5e4374255aaf5b70ac1f64636
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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