Diisopropylamine → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2099362노트

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HRID 2099362 반응식
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([OH:13])=O.Cl.[CH3:22][N:23](C)[OH:24].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCC[CH2:36]1.C(NC(C)C)(C)C>ClCCl.C(OCC)(=O)C>[CH3:36][O:24][N:23]([CH3:22])[C:11]([C@H:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][N:1]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:13]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 688607(3R)-2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 2733179PyBroP

생성물 1

HCID 86597541(3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate수율 92.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

6.95 g of Boc-D-Tic-OH are dissolved in 25 ml of dichloromethane. 2.69 g of dimethylhydroxylamine hydrochloride and 11.68 g of bromotrispyrrolidino-phosphonium hexafluorophosphate are added. After cooling of the solution to 0° C., 9.72 ml of diisopropylamine are slowly added. The reaction medium is then stirred at ambient temperature for 16 h. After hydrolysis, extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. Drying over MgSO4 and concentration to dryness are carried out. The crude obtained is chromatographed on silica gel, elution being carried out with a 99/1 mixture of dichloromethane and methanol. 7.4 g of tert-butyl (3R)-3-{[methoxy(methyl)amino]carbonyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate are obtained.

후처리

  1. customAfter hydrolysis, extraction
  2. dry with materialDrying over MgSO4 and concentration to dryness
  3. customThe crude obtained
  4. customis chromatographed on silica gel, elution
  5. additionbeing carried out with a 99/1 mixture of dichloromethane and methanol

출처 및 근거

ORD 기록
ord-0f9a7043712d4c6d9f1ed3657a2c4f6c
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569582B2

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