참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Nitrogen | HCID 947 | — |
| 반응물 | Vinyloxirane | HCID 13586 | — |
| 반응물 | Tert-butyl N-(benzyloxy)carbamate | HCID 736159 | — |
| 촉매 | Tetrabutylammonium Bromide | HCID 74236 | — |
| 촉매 | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| 용매 | Acetonitrile | HCID 6342 | — |
| 생성물 | (R)-tert-butyl benzyloxy(1-hydroxybut-3-en-2-yl)carbamate | HCID 89852321 | 93% |
반응 단계
In a 3 L RBF, a solution of tert-butyl benzyloxycarbamate (Intermediate 153, 86.9 g, 389.22 mmol), N,N(1S,2S)-cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (18.5 g, 23.39 mmol), Pd2(dba)3-CHCl3 (8.05 g, 7.78 mmol) and TBAB (150.5 g, 466.81 mmol) in acetonitrile (1.8 L) was bubbled with N2 for 30 minutes and the flask was closed with a rubber septum. The solution was then kept in a −20° C. freezer for 2 hrs. 2-vinyloxirane (30 g, 428.02 mmol, 1.10 equiv) was added and the mixture was stirred in the freezer (−20-25° C.) for 3 days. The mixture was filtered and the filtrate was evaporated. The residue was purified by silica gel column eluted with EtOAc/hexane (0-40%) to give the title compound (106 g, 93%) as a pale yellow oil.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09309245B2 |
|---|
| 출처 데이터셋 | uspto-grants-2016_04 |
|---|
| ORD ID | ord-acb24115ddb249fe8edce1770a1d3d32 |
|---|
| 출처 메모 | uspto-grants-2016_04 |
|---|
