(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate → Methyl (1S,3S)-3-hydroxycyclopentanecarboxylate

반응식

[C@@H:1]12[O:6][C@@H:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]2>CC(OC)(C)C>[OH:6][C@H:1]1[CH2:5][CH2:4][C@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

참가 물질

실험 절차

A solution of methyl (1S,5R)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (8 g, 56.3 mmol) in MTBE (100 ml) was hydrogenated at 3 atm on Parr shaker for 12 hrs. Filtered through celite evaporated followed by chromatagraphy on a 50 g silica gel Biotage Snap cartridge with 10-50% 6:3:1 Hexane-MTBE-MeCN/Hexane to give title compound. 1H NMR (500 MHz, CDCl3) δ 1.63-1.74 (m, 3H), δ 1.78 (s, br, 1H), δ 1.82-2.07 (m, 4H), δ 2.11-2.19 (m, 1H), δ 3.09 (m, 1H), δ 3.70 (s, 3H), δ 4.48 (m, 1H)

후처리

filtrationFiltered through celite
customevaporated

출처 및 근거

ORD 기록: ord-322b1f56ae174129abd8188c9fa41142
출처 데이터셋: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08119806B2

반응 노트

불러오는 중…

참가 물질

반응물 1

HCID 10374550(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate

생성물 1

HCID 10986356Methyl (1S,3S)-3-hydroxycyclopentanecarboxylate

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

후처리

filtrationFiltered through celite
customevaporated

출처 및 근거

ORD 기록: ord-322b1f56ae174129abd8188c9fa41142
출처 데이터셋: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08119806B2

반응 노트

불러오는 중…