Carbon tetrabromide → HCID 14756526, compound

HRID 1911527Notes

Reaction equation

HRID 1911527 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=O)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36](Br)(Br)([Br:38])[Br:37]>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=[C:36]([Br:38])[Br:37])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-

Product 1

HCID 14756526HCID 14756526, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution of (R)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (4.30 g; CAS 95715-87-0 and triphenylphosphine (9.15 g) in dichloromethane (100 ml) was added portionwise carbon tetrabromide (6.94 g). The mixture was stirred at 0° C. for 20 min and then at r.t. for 2 h. The mixture was concentrated in vacuo to ca 20 ml, then diluted with hexane (100 ml) and concentrated in vacuo to half-volume. The residue was stirred at 0° C. for 15 min, then the mixture was filtered and the filtrate was concentrated in vacuo to afford (S)-4-(2,2-dibromo-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (6.18 g, 92%) as a colourless oil. MS (EI): 330.9 ([{81Br}M—C4H8]+), 328.9 ([{81 Br79 Br}M—C4H8]+), 326.9 ([{79 Br}M—C4H8]+).

Workup

  1. waitat r.t. for 2 h
  2. concentrationThe mixture was concentrated in vacuo to ca 20 ml
  3. additiondiluted with hexane (100 ml)
  4. concentrationconcentrated in vacuo to half-volume
  5. stirringThe residue was stirred at 0° C. for 15 min
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4eb1522ad31c462284cbc54627185f7e
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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