Pyridine → HCID 57552215, compound

HRID 1986897Notes

Reaction equation

HRID 1986897 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:28][CH:29]([CH2:39]O)[CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].N1C=CC=CC=1>ClCCl>[Br:8][CH2:39][CH:29]([F:28])[CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 6420752tert-Butyl 2-fluoro-3-hydroxypropylcarbamate

Product 1

HCID 57552215HCID 57552215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of NBS (20 g, 110 mmol, 3.0 equiv) in dichloromethane (250 mL) was added dropwise triphenylphosphine (28 g, 110 nmol, 3.0 equiv) in dichloromethane (100 mL). After addition was complete, the reaction mixture was stirred for 10 min and a solution of tert-butyl 2-fluoro-3-hydroxypropylcarbamate (1-8) (7.0 g, 36 mmol, 1 equiv) in dichloromethane (100 mL) followed by pyridine (3.5 g, 44 mmol, 1.2 equiv) were added. The resulting mixture was stirred at 23° C. under nitrogen for 16 h. The reaction solution was concentrated and purified by silica gel chromatography (100% hexanes to 100% ethyl acetate over 1 h, analysis by Ninhydrin stain) to yield tert-butyl 3-bromo-2-fluoropropylcarbamate (1-9) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 4.89-4.68 (m, 2H), 3.55-3.40 (m, 2H), 1.45 (s, 9H).

Workup

  1. additionAfter addition
  2. additionwere added
  3. stirringThe resulting mixture was stirred at 23° C. under nitrogen for 16 h
  4. concentrationThe reaction solution was concentrated
  5. custompurified by silica gel chromatography (100% hexanes to 100% ethyl acetate over 1 h, analysis by Ninhydrin stain)

Sources & evidence

ORD record
ord-d091299902bf4fbca2ddd50b77958d5e
Source dataset
uspto-grants-2009_06
Patent number
US07550477B2

Reaction notes

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