Tetrabutylammonium Fluoride → HCID 21919449, compound

HRID 1244690Notes

Reaction equation

C[Si](C)(C)CCOC(=O)[NH:7][CH:8]1[CH2:25][N:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:11]2[CH2:10][CH:9]1[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:30]([O:29][C:27](=[O:28])[NH:26][CH:9]1[CH:8]([NH2:7])[CH2:25][N:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:11]2[CH2:10]1)=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)([CH3:33])([CH3:31])[CH3:32]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 68621280HCID 68621280, compound

Product 1

HCID 21919449HCID 21919449, compoundYield 95.1%

Conditions

Temperature: 50 °C

Procedure

A suspension of (RS,RS,RS)-(2-tert-butoxycarbonylamino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (5.22 g, 10.0 mmol) in tetrabutylammonium fluoride solution (1 M in THF, 42 mL, 42 mmol) was heated 90 min at 50° C. The resultant solution was concentrated in vacuo and chromatographed (CH2Cl2/MeOH/NH4OH 95:5:0.25) to afford the title compound (3.59 g, 95%). Light yellow solid, MS (ISP) 378.4 (M+H)+; tR=7.2 and 18.9 min (Chiralpak® AD 25×0.03 cm, heptane/ethanol/triethylamine 70:30:0.3, flow rate 4 μL/min).

Workup

concentrationThe resultant solution was concentrated in vacuo
customchromatographed (CH2Cl2/MeOH/NH4OH 95:5:0.25)

Sources & evidence

ORD record: ord-3d93ae0eaef24b878c28c072711b2f1c
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122555B2

Reaction notes

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