Formaldehyde → HCID 66671610, compound

HRID 446492Notes

Reaction equation

HRID 446492 reaction equation
[CH2:1]=O.[NH2:3][CH2:4][C@@:5]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([OH:16])[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].O>C1C=CC=CC=1>[Si:9]([O:8][CH2:7][CH2:6][C@:5]1([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[O:16][CH2:1][NH:3][CH2:4]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 66671624HCID 66671624, compound

Product 1

HCID 66671610HCID 66671610, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Paraformaldehyde (18.50 g, 0.617 mol) was added to a solution of (2R)-1-amino-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-fluorophenyl)butan-2-ol (128.92 g, 0.411 mol) in benzene (1000 mL), a water separator was mounted, and the mixture was stirred at reflux temperature for 4 hours. The reaction mixture was concentrated under reduced pressure to give 139.43 g of crude (5R)-5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-(4-fluorophenyl)-1,3-oxazolidine as a brown oily substance.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb6071eb591a44b88a8ed4ad50acd1da
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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