Tetrabutylammonium Fluoride → (R)-2-tert-butyl 1-methyl 6-(3-hydroxybenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate

HRID 1710882Notes

Reaction equation

HRID 1710882 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][Si](C(C)(C)C)(C)C.[OH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C@H:24]([C:28]([O:30][CH3:31])=[O:29])[N:23]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:22][CH2:21]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[OH:6][C:5]1[CH:4]=[C:3]([CH:16]=[CH:15][CH:14]=1)[CH2:2][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C@H:24]([C:28]([O:30][CH3:31])=[O:29])[N:23]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:22][CH2:21]2

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 10040514[3-(Bromomethyl)phenoxy](tert-butyl)dimethylsilaneHCID 58858237(R)-2-tert-butyl 1-methyl 6-hydroxy-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate

Product 1

HCID 16222231(R)-2-tert-butyl 1-methyl 6-(3-hydroxybenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate

Procedure

Example 4 was synthesized from (3-(bromomethyl)phenoxy)(tert-butyl)dimethylsilane and (R)-2-tert-butyl 1-methyl 6-hydroxy-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate using a similar procedure as described in procedure 2, followed by tetrabutylammonium fluoride deprotection. HPLC retention time (Method c)=3.75 min. LC/MS (ESI) (M+H)+=436.20. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (s, 4H), 1.49 (s, 5H), 2.73-2.99 (m, 2H), 3.62-3.83 (m, 2H), 3.69 (s, 3H), 5.00 (s, 2H), 5.12 (brs, 1H), 5.35 (d, J=14.65 Hz, 0.5H), 5.52 (d, J=7.07 Hz, 0.5H), 6.74-6.97 (m, 3H), 6.89-6.93 (m, 1H), 6.96 (d, J=8.08 Hz, 1H), 7.23 (d, J=7.83 Hz, 1H), 7.37 (dd, J=8.59, 4.29 Hz, 1H).

Workup

  1. customHPLC retention time (Method c)=3.75 min

Sources & evidence

ORD record
ord-b0d2d064bd1a4d598573d41bf7995936
Source dataset
uspto-grants-2010_09
Patent number
US07790745B2

Reaction notes

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