(R)-2-Methyl-CBS-oxazaborolidine → HCID 68679478, compound

HRID 2353977Notes

Reaction equation

HRID 2353977 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[O:16][C:17]([F:23])([F:22])[O:18][C:19]=3[CH:20]=2)[C:12](=[O:24])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.C(OCC)(=O)C.CCCCCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[O:16][C:17]([F:23])([F:22])[O:18][C:19]=3[CH:20]=2)[C@H:12]([OH:24])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 12423031(Dimethyl sulfide)trihydroboronHCID 21226206Ethyl acetate hexaneHCID 68680031HCID 68680031, compound

Product 1

HCID 68679478HCID 68679478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Add a solution of 2,2-Difluoro-9-oxo-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (2.2 mmol) in THF (20 mL), to a cooled (−78° C.) solution of Borane-methyl sulfide (2.6 mmol) and (R)-2-methyl-CBS-oxazaborolidine (3.3 mmol) in THF (20 mL). After warming slowly to 0° C. for 1 h, quench the reaction with methanol (2 mL). Remove solvent under vacuum and chromatograph using ethyl acetate/hexane (2-35%) to elute. This gives the title compound as a colorless solid.

Workup

  1. customquench
  2. customthe reaction with methanol (2 mL)
  3. washto elute

Sources & evidence

ORD record
ord-062584c42132429a94709325de8dba74
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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