Thiophene-3-methanol → HCID 22126838, compound

HRID 1005180Notes

Reaction equation

HRID 1005180 reaction equation
C([C:5]1([O:11][CH2:12][CH2:13][CH2:14]Br)[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)(C)(C)C.[OH:16][CH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1>CN(C=O)C>[S:20]1[CH:21]=[CH:22][C:18]([CH2:17][O:16][CH2:14][CH2:13][CH2:12][O:11][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)=[CH:19]1

Participants

4

Reactant 2

HCID 123570Thiophene-3-methanolHCID 86604480HCID 86604480, compound

Product 1

HCID 22126838HCID 22126838, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an analogous manner to that described in Example 1 (g), by alkylating tert-butyl (RS)-2-(3-bromo-propoxy)-tetrahydro-pyran with 3-hydroxymethyl-thiophene in DMF there was obtained (RS)-2-[3-(thiophen-3-ylmethoxy)-propoxy]-tetrahydro-pyran, which after cleavage of the THP group analogously to Example 53 (c) yielded 3-(thiophen-3-ylmethoxy)-propan-1-ol. Subsequent conversion into the mesylate according to a procedure known from the literature and alkylation therewith effected analogously to Example 44 (e) of tert-butyl (3RS,4RS)-3-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate [Example 46 (b)] gave tert-butyl (3RS,4RS)-3-hydroxy-4-[4-[3-(thiophen-3-ylmethoxy)-propoxy]-phenyl]-piperidine-1-carboxylate. By alkylation with 2-chloromethyl-1,4-dimethoxy-naphthalene analogously to Example 1 (g) there was obtained tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-{4-[3-(thiophen-3-ylmethoxy)-propoxy]-phenyl}-piperidine-1-carboxylate as a pale yellow solid; MS: 648 (M+H)+.

Sources & evidence

ORD record
ord-e126f92e287b4405b23cb1bf3daa4f53
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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