Sodium triacetoxyborohydride → (S)-N-(3,4-Dimethyl-phenyl)-2-(oxetan-3-ylamino)-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094406Notes

Reaction equation

HRID 1094406 reaction equation
[NH2:1][C@@H:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:3]([N:5]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([CH3:25])[CH:19]=1)[CH2:6][CH2:7][C:8]1[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1)=[O:4].[O:32]1[CH2:35][C:34](=O)[CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:25][C:20]1[CH:19]=[C:18]([N:5]([CH2:6][CH2:7][C:8]2[CH:9]=[N:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)[C:3](=[O:4])[C@@H:2]([NH:1][CH:34]2[CH2:35][O:32][CH2:33]2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:23]=[CH:22][C:21]=1[CH3:24]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 44546187(S)-2-amino-N-(3,4-dimethyl-phenyl)-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Product 1

HCID 44546378(S)-N-(3,4-Dimethyl-phenyl)-2-(oxetan-3-ylamino)-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 25 mg (S)-2-Amino-N-(3,4-dimethyl-phenyl)-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide (from example 1) in 1.5 ml dry CH2Cl2 under argon in a sealed tube was added 1.1 eq. oxetan-3-one. The reaction mixture was stirred at RT for 20 min, followed by the addition of 3.0 eq., Sodium triacetoxyborohydride and the reaction stirred for 16 h at RT. The reaction mixture diluted with 10 ml CH2Cl2 and washed with 2M aq. Na2CO3 2M, dried and concentrated then chromatographed on silica gel (EtOAc/Heptane, gradient elution) to give the desired compound. MS(m/e): 484.2 [M+H]+.

Workup

  1. stirringthe reaction stirred for 16 h at RT
  2. washwashed with 2M aq. Na2CO3 2M
  3. customdried
  4. concentrationconcentrated
  5. customthen chromatographed on silica gel (EtOAc/Heptane, gradient elution)

Sources & evidence

ORD record
ord-24bb3c79a27a4d7fbe5f11337857835d
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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