Methanol → (R)-methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

HRID 528858Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([C:11]([OH:13])=[O:12])[NH:2]1.O=S(Cl)[Cl:16].[CH3:18]O>>[ClH:16].[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]([C:11]([O:13][CH3:18])=[O:12])[NH:2]1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 71060992(R)-methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochlorideYield 71%

Procedure

To (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Aldrich, 500 mg, 2.82 mmol) in MeOH (2.8 mL) was added SOCl2 (824 μL, 11.3 mmol) at 0° C. The resulting reaction mixture was allowed to warm to room temperature over 5 h and then stirred at 50° C. overnight. The reaction mixture was then concentrated in vacuo to give the title compound (457 mg, 71%) as a white solid. 1H NMR (CDCl3) δ 7.30-7.23 (m, 2H), 7.20-7.13 (m, 2H), 4.78-4.69 (m, 1H), 4.56-4.45 (m, 1H), 4.43-4.35 (m, 1H), 3.87 (s, 3H), 3.49-3.43 (m, 2H); MS(ESI+) m/z 192.1 (M+H)+.

Workup

customThe resulting reaction mixture
concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-e4b3a9d86ea74046a8e5c91590b95c0b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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