(R)-tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)pent-4-en-2-yl)carbamate → (R)-1((2-(Bromomethyl)benzyl)oxy)pent-4-en-2-amine

HRID 1429383Notes

Reaction equation

HRID 1429383 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:20][CH:21]=[CH2:22])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][Br:19])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:19][CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][O:10][CH2:9][C@H:8]([NH2:7])[CH2:20][CH:21]=[CH2:22]

Participants

3

Reactant 1

HCID 68233279(R)-tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)pent-4-en-2-yl)carbamate

Product 1

HCID 68233277(R)-1((2-(Bromomethyl)benzyl)oxy)pent-4-en-2-amineYield 98%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of compound 18j (2.8 g, 7.3 mmol) in TFA/DCM (25 mL, v/v=1/4) was stirred at rt for 1 hr. The mixture was concentrated under reduced pressure to give compound 18k (2.0 g, 98% yield), which was used without purification. LCMS (m/z): 285.1 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1d3db3e29cd4390b6c6110979fd38dc
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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