Methanol → HCID 70160912, compound

HRID 2227276Notes

Reaction equation

HRID 2227276 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.B.CSC.[C:26]([O:30][C:31](=[O:53])[NH:32][C@H:33]1[CH2:37][C@@H:36]([CH3:38])[N:35]([CH2:39][C:40](=[O:51])[CH:41]=[CH:42][C:43]2[CH:44]=[N:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=2)[C:34]1=[O:52])([CH3:29])([CH3:28])[CH3:27].CO>ClCCl.C1COCC1>[C:26]([O:30][C:31](=[O:53])[NH:32][C@H:33]1[CH2:37][C@@H:36]([CH3:38])[N:35]([CH2:39][C@H:40]([OH:51])[CH:41]=[CH:42][C:43]2[CH:44]=[N:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=2)[C:34]1=[O:52])([CH3:27])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 887MethanolHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboronHCID 70160415HCID 70160415, compound

Product 1

HCID 70160912HCID 70160912, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-methyl-CBS-oxazaborolidine (4.47 mL, 1M in toluene) in dichloromethane (10 mL) was added a solution of borane-dimethylsulfide (0.45 mL, 10M) and the resulting solution was stirred at ambient temperature for 40 minutes. This solution was added to a stirred solution of 4-4 (580 mg, 1.49 mmol) in THF (15 mL) at −40° C. and the reaction mixture was stirred for 3 hours. Methanol (2 mL) was added and the reaction mixture was concentrated at reduced pressure. The residue was purified by flash column chromatography (silica gel, 2:1 ethyl acetate/hexanes) to give 4-5 as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours
  2. concentrationthe reaction mixture was concentrated at reduced pressure
  3. customThe residue was purified by flash column chromatography (silica gel, 2:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-11e428ecabeb4bdca2a743e3a38872f2
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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