Trifluoroacetic acid → Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

참여 물질

역할	이름	HCID	투입량
반응물	Trifluoroacetic acid	HCID 6422	—
반응물	Carbonic acid--N,N-diethylethanamine (1/2)	HCID 15264167	—
반응물	rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylate	HCID 59254350	—
반응물	1,1-dimethylethyl (3R,4R)-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate	HCID 59254362	—
용매	Methanol	HCID 887	—
용매	Dichloromethane	HCID 6344	—
생성물	Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate	HCID 86616784	100%

반응 단계

To a stirred solution of 1,1-dimethylethyl (3R,4R)-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (for a synthesis see WO2006002047, Preparation 24(c) (±)-1,1-dimethylethyl cis-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate E2 isomer) (2 g, 5.7 mmol) in DCM (50 ml) was added trifluoracetic acid (50 mL) and stirred for 2 h. The reaction mixture was concentrated and placed under high-vac for 3 h. To the TFA salt dissolved in 100 ml of 10:1 CHCl3:MeOH was added MP-carbonate resin (8 g; 22.8 mmol) and stirred overnight. The reaction mixture was filtered and concentrated to provide the title compound as a pale yellow oil (1.4 g; 100%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08071592B2
출처 데이터셋	uspto-grants-2011_12
ORD ID	ord-c369e84b488d4732a9fca5b03667e7ed
출처 메모	uspto-grants-2011_12