Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → 1,1-Dimethylethyl 4-(2H-tetrazol-2-ylmethyl)-1-piperidinecarboxylate

HRID 412880Notes

Reaction equation

HRID 412880 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH:20]=[N:19][N:18]=[N:17]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:17]2[N:18]=[N:19][CH:20]=[N:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:16]2[CH:20]=[N:19][N:18]=[N:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178418441HCID 178418441, compound

Product 2

HCID 185384341,1-Dimethylethyl 4-(2H-tetrazol-2-ylmethyl)-1-piperidinecarboxylateHCID 18539148HCID 18539148, compound

Procedure

By a similar manner to Reference Example 29, 1-tert-butoxycarbonyl-piperidin-4-methanol (2.15 g, 10.0 mmol) was reacted with 1H-tetrazole (2.10 g, 30 mmol) to give 1-tert-butoxycarbonyl-4-(2H-tetrazol-2-ylmethyl)piperidine as pale yellow oily substance (1.35 g, 50%) and 1-tert-butoxycarbonyl-4-(1H-tetrazol-1-ylmethyl)piperidine as pale yellow solid substance (1.23 g, 46%).

Sources & evidence

ORD record
ord-71225d3164a64fb5828f471c2efa623a
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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