Ammonium Chloride → Tert-butyl (3s,5s,6r)-3-allyl-2-oxo-5,6-diphenyl-3-[1-(2-trimethylsilanyl-ethoxycarbonyl)piperidin-4-ylmethyl]morpholine-4-carboxylate

HRID 1743267

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HRID 1743267 반응식
[CH2:1]([C@H:4]1[C:9](=[O:10])[O:8][C@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:2]=[CH2:3].C1OCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:56][CH:57]1[CH2:62][CH2:61][N:60]([C:63]([O:65][CH2:66][CH2:67][Si:68]([CH3:71])([CH3:70])[CH3:69])=[O:64])[CH2:59][CH2:58]1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([C@:4]1([CH2:56][CH:57]2[CH2:62][CH2:61][N:60]([C:63]([O:65][CH2:66][CH2:67][Si:68]([CH3:69])([CH3:71])[CH3:70])=[O:64])[CH2:59][CH2:58]2)[C:9](=[O:10])[O:8][C@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:2]=[CH2:3]

참가 물질

7

반응물 5

HCID 25517Ammonium ChlorideHCID 3633615-Crown-5HCID 2724254Sodium bis(trimethylsilyl)amideHCID 11058313Tert-butyl (3s,5s,6r)-3-allyl-2-oxo-5,6-diphenylmorpholine-4-carboxylateHCID 222383942-Trimethylsilanylethyl 4-bromomethyl-piperidine-1-carboxylate

생성물 1

HCID 91566876Tert-butyl (3s,5s,6r)-3-allyl-2-oxo-5,6-diphenyl-3-[1-(2-trimethylsilanyl-ethoxycarbonyl)piperidin-4-ylmethyl]morpholine-4-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

4.9 g of tert-butyl (3S,5S,6R)-3-allyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate were dissolved in 100 ml of THF. 14.9 ml of 15-crown-5 were added, and the mixture was cooled to −78° C. Then 6.8 ml of a 2 M solution of NaHMDS in THF were added dropwise. The mixture was stirred for 10 min and then 8 g of 2-trimethylsilanylethyl 4-bromomethylpiperidine-1-carboxylate were added dropwise. The mixture was allowed to warm to 0° C. over the course of 6 h, and the reaction was then stopped by adding 500 ml of saturated ammonium chloride solution. The aqueous phase was extracted 3 times with 400 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.

후처리

  1. temperatureto warm to 0° C. over the course of 6 h
  2. extractionThe aqueous phase was extracted 3 times with 400 ml of ethyl acetate each time
  3. dry with materialthe combined organic phases were dried with MgSO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-c763f98885134e59bb54f39f86b5311f
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07008957B2

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