Formaldehyde → (RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[CH2:12]=O>>[S:1]1[C:2]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[NH:8][CH2:12][C:3]=2[CH:4]=[CH:5]1

Participants

Reactant 2

HCID 712Formaldehyde

HCID 146719beta-2-Thienyl-L-alanine

Product 1

HCID 12685848(RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Conditions

Temperature: 60 °C

Procedure

A suspension of (D,L) 3-(2-thienyl)-alanine (302 mg, 1.77 mmol) in 37% aq. HCHO (4 mL) was heated at 60° C. for 2 h. The suspension became clear. It was concentrated in vacuo to give the titled compound (323 mg), which was used in the next step without further purification. MS 184.3 (M+H)

Workup

concentrationIt was concentrated in vacuo

Sources & evidence

ORD record: ord-a8f032a3ef6c42788b3757bfadf6681b
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612089B2

Reaction notes

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