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

HRID 2099362Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-0f9a7043712d4c6d9f1ed3657a2c4f6c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569582B2

Reaction notes

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