Hydrogen Bromide → HCID 46938159, compound

HRID 1963356Notes

Reaction equation

HRID 1963356 reaction equation
Br.[CH:2]1([CH2:8][C@@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2C(OC)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>>[CH:2]1([CH2:8][C@@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][NH:10]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 66732142HCID 66732142, compound

Product 1

HCID 46938159HCID 46938159, compoundYield 25%

Procedure

HBr (33% in acetic acid) (5 mL) was added to (2R,4R)-methyl 2-(cyclohexylmethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.28 g, 0.87 mmol). The reaction was stirred vigorously overnight. The solvent was evaporated. Purification using PrepLC (pH=11, small column, no sandwitching, sample dissolved in methanol/water (50/50), gradient 15-55, 20 minutes). The title compound (57 mg, 25%) was obtained. 1H NMR (400 MHz, cd3od) δ 0.78-0.95 (m, 2H), 1.17 (dd, 3H), 1.28-1.48 (m, 4H), 1.63 (dd, 6H), 2.04 (d, 1H), 2.12 (d, 1H), 2.85 (t, 1H), 2.96 (dd, 1H), 3.13 (s, 1H), 3.31 (d, 1H), 5.40 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. customPurification
  3. dissolutionno sandwitching, sample dissolved in methanol/water (50/50)
  4. customgradient 15-55, 20 minutes

Sources & evidence

ORD record
ord-d6f89293c5504738a09d9b383543b46d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…