Aluminium lithium hydride → HCID 70200310, 화합물

HRID 861353노트

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HRID 861353 반응식
C[O:2][C:3]([CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[N:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:3][CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[N:21]=[CH:22][C:23]([F:26])=[CH:24][N:25]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 57016126HCID 57016126, 화합물

생성물 1

HCID 70200310HCID 70200310, 화합물수율 63%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 0.13 g (0.33 mmol) of (7S,8aS)-7-(4-((methoxycarbonyl)methyl)phenoxy)methyl-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Example 11i) in 15 mL of anhydrous ethyl ether was added dropwise to an ice-cold suspension of 0.025 g (0.65 mmol) of lithium aluminum hydride in 15 mL of anhydrous ethyl ether and the mixture stirred for 30 min. The reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 mL of water. The precipiate which formed was filtered through Celite, the filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 ethyl acetate:methanol gave 0.075 g (63%) of the title compound. mp (.HCl) 145°-147° C. HRMS calcd for C20H26FN4 O2 (MH+): 373.2040, found: 373.2054.

후처리

  1. customThe reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 mL of water
  2. customThe precipiate which formed
  3. filtrationwas filtered through Celite
  4. concentrationthe filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 ethyl acetate

출처 및 근거

ORD 기록
ord-12b82b0127504299966061e250f6691f
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714487

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