HCID 86602761, compound → HCID 86602760, compound

HRID 349721Notes

Reaction equation

HRID 349721 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][O:7][CH2:8][C@:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:15][Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:10]=[CH:11][N+:12]([O-])=O>[Pt](=O)=O.CO>[F:36][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][O:7][CH2:8][C@:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:15][Si:16]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:17][CH3:18])[CH2:10][CH2:11][NH2:12]

Participants

4

Reactant 1

HCID 86602761HCID 86602761, compound

Product 1

HCID 86602760HCID 86602760, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent3×

Procedure

A flask was charged with (S)-(1-(3,5-bis(trifluoromethyl)benzyloxy)-4-nitro-2-phenylbut-3-en-2-yloxy)triethylsilane (35 mg, 64 μmol), methanol (1.5 mL), and platinum dioxide (20 mg, 88 μmol). The flask was purged with hydrogen and stirred under a balloon of hydrogen for 2 h. The reaction was filtered through celite and concentrated. Column chromatography (5% methanol/dichloromethane) gave 20 mg (60%) as a colorless oil. Retention time: 1.98 min. (Phenomenex C18 3.0×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=2 min., Flow rate=5 mL/min.) Mass spec.: 522.16 (MH)+.

Workup

  1. customThe flask was purged with hydrogen
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated
  4. customColumn chromatography (5% methanol/dichloromethane) gave 20 mg (60%) as a colorless oil

Sources & evidence

ORD record
ord-e6779d72d899470588ba239b7269f59b
Source dataset
uspto-grants-2007_02
Patent number
US07179926B2

Reaction notes

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