Carbon tetrabromide → HCID 68809313, compound

HRID 434290Notes

Reaction equation

HRID 434290 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:9]O)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:9][Br:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68810908HCID 68810908, compound

Product 1

HCID 68809313HCID 68809313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((R)-2-hydroxy-1-pyridin-3-ylmethyl-ethyl)-carbamic acid tert-butyl ester (0.43, 1.70 mmol) in dichloromethane (10 ml) is added carbon tetrabromide (0.33 g), 2.04 mmol) and triphenylphosphine (0.23 g, 1.70 mmol). The reaction mixture is stirred at ambient temperature for 2 hours, filtered, and the filtrate partioned between ethylacetate and hydrochloric acid (1M). The aqueous phase is separated, neutralised with saturated sodium bicarbonate solution and extracted into dichloromethane. The dichloromethane is dried over magnesium sulphate and evaporated to afford ((R)-2-bromo-1-pyridin-3-ylmethyl-ethyl)-carbamic acid tert-butyl ester. 1H NMR (400 MHz, CDCl3) δ 1.29 (s 9H), 3.05 (dd J 14.3 9.8 1H), 3.18 (dd J 14.3 4.9 1H), 3.51 (d J 4.9 2H) 4.07-4.16 (m 1H) 7.84 (dd J 7.9 5.9 1H), 8.35 (d J 7.9 1H), 8.65 (d, J 5.4 1H), 8.86 (s, 1H).

Workup

  1. filtrationfiltered
  2. customThe aqueous phase is separated
  3. extractionextracted into dichloromethane
  4. dry with materialThe dichloromethane is dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-e93cc66c4c4e406b95cf463ed62ed253
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

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