tert-Butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate → HCID 21912742, compound

HRID 1245610Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]([CH2:19][CH3:20])[N:17]=[C:16]([CH2:21][O:22]CC3C=CC=CC=3)[C:15]=2[CH3:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC(C(Br)C=O)CC1)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]([CH2:19][CH3:20])[N:17]=[C:16]([CH2:21][OH:22])[C:15]=2[CH3:30])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 21912701tert-Butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate

HCID 21912793HCID 21912793, compound

Product 1

HCID 21912742HCID 21912742, compound

Procedure

The title compound was prepared from 1-(tert-butoxycarbonyl)-4-(1-ethyl-3-benzyloxymethyl-4-methyl-(1H)-pyrazol-5-yl)piperidine (from Step B) using a procedure analogous to that described for Pyrrolidine 1, Step E. RF: 0.21 (3:2 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.36 (t, J=7.2, 3H), 1.48 (s, 9H), 1.67–1.70 (m, 2H), 1.84–1.93 (m, 2H), 2.08 (s, 3H), 2.74–2.80 (m, 3H), 3.14 (br m, 1H), 4.10 (q, J=7.2, 2H), 4.12–4.26 (m, 2H), 4.59 (s, 2H).

Sources & evidence

ORD record: ord-be26f8dc7d9542cdb43fb6b99b5a9058
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125887B2

Reaction notes

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