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

HRID 2099362ノート

反応式

HRID 2099362 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f9a7043712d4c6d9f1ed3657a2c4f6c
出典データセット
uspto-grants-2009_08
特許番号
US07569582B2

反応ノート

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