Water → (R)-tert-butyl 1-bromopropan-2-ylcarbamate

HRID 1844399Notes

Reaction equation

HRID 1844399 reaction equation
O[CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(Cl)Cl>[Br:14][CH2:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 57081792(R)-tert-butyl 1-bromopropan-2-ylcarbamateYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-tert-Butyl 1-hydroxypropan-2-ylcarbamate (1 g, 5.71 mmol) and carbon tetrabromide (2.84 g, 8.56 mmol) were stirred in CH2Cl2 (20 mL) at −20° C. under argon. A solution of triphenylphosphine (2.40 g, 9.13 mmol) in CH2Cl2 (5 mL) was added dropwise. The reaction was allowed to reach rt and stirred for 14 h. H2O (50 mL) was added to the reaction mixture and the aqueous layer was removed and the CH2Cl2 layer was dried over Na2SO4, filtered, and evaporated. The residue was applied to a silica ISCO column and eluted with 5:1 hexanes/EtOAc. Intermediate 5A (0.68 g, 2.86 mmol, 50.0% yield) was isolated as a white solid. LC-MS (ESI) 183.9 (M−tBu+H), RT=1.76 min (Method B).

Workup

  1. customto reach rt
  2. customthe aqueous layer was removed
  3. dry with materialthe CH2Cl2 layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. washeluted with 5:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-f5cce0b148ec4b1f8187b3a969ec9ea9
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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