3-(Trifluoromethoxy)aniline → HCID 68283518, compound

HRID 1527538Notes

Reaction equation

HRID 1527538 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH:10]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][C:16]([F:15])([F:25])[F:26])[CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 737533-(Trifluoromethoxy)anilineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68283518HCID 68283518, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-L-prolinal (200 mg, 1.00 mmol) and 3-trifluoromethoxy-phenylamine (186.8 mg, 1.05 mmol) were mixed in 1,2-dichloroethane (10 mL) and treated with sodium triacetoxyborohydride (314 mg, 1.41 mmol). The mixture was stirred at RT under nitrogen overnight, then quenched by addition of water, extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated. The crude oil was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1) to give the desired material. MS (LC/MS): 361.1 [M+H]+.

Workup

  1. customquenched by addition of water
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-db17d04a1523400bad8c6b5b4d5f6a58
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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