n-Cbz-(1r)-1-[(rs)-(5-tert-butyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine → (1R)-1-[(RS)-(5-tert-Butyl-2-benzoxazolyl)hydroxymethl]-3-phenylpropylamine

HRID 2304866Notes

Reaction equation

HRID 2304866 reaction equation
C([NH:11][C@@H:12]([CH:21]([C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][C:26]=2[N:27]=1)[OH:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(OCC1C=CC=CC=1)=O>[Pd].CO>[C:32]([C:29]1[CH:30]=[CH:31][C:25]2[O:24][C:23]([CH:21]([OH:22])[C@H:12]([NH2:11])[CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:27][C:26]=2[CH:28]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 1

HCID 22961342n-Cbz-(1r)-1-[(rs)-(5-tert-butyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine

Product 1

HCID 57124382(1R)-1-[(RS)-(5-tert-Butyl-2-benzoxazolyl)hydroxymethl]-3-phenylpropylamineYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-CBz-(1R)-1-[(RS)-(5-tert-butyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine (360 mg), anhydrous methanol (8 ml), and 10% palladium-on-charcoal (40 mg) was degassed, under reduced pressure, and then stirred vigorously under hydrogen atmosphere for 10 h. The mixture is filtered on a nylon pad (0.45 μm porosity) and concentrated in vacuo to afford the title product (210 mg) as a clear oil: 1H NMR (400 MHz, CDCl3, 3:2 mixture of diastereomers) δ 1.80-2.02 (m, 2H), 2.65-2.89 (m, 2H), 3.23 (m, 0.4H), 3.39 (m, 0.6H), 4.76 (d, J=1.8 Hz, 0.6H), 4.84 (d, J=2.4 Hz, 0.4H), 7.09 (m, 3H), 7.29 (m, 2H), 7.43 (m, 2H), and 7.76 (s, 1H).

Workup

  1. customwas degassed, under reduced pressure
  2. filtrationThe mixture is filtered on a nylon pad (0.45 μm porosity)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9527de8ce2849628d7b96d4bfb2e375
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

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