tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 68109270, compound

HRID 2179344Notes

Reaction equation

HRID 2179344 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[O:10]N.O=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>>[F:2][C:3]1[C:4]2[O:10][C:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]=3[C:5]=2[CH:6]=[C:7]([Br:9])[CH:8]=1

Participants

3

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 68109038HCID 68109038, compound

Product 1

HCID 68109270HCID 68109270, compoundYield 14%

Procedure

The product of step A was reacted with tert-butyl 4-oxopiperidine-1-carboxylate then Boc protected following the procedure of Example 29, step B. Purification by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) provided tert-butyl 6-fluoro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (320 mg, 14%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.33 (s, 1H), 7.16 (dd, J=10.0, 1.6 Hz, 1H), 4.51 (br s, 2H), 3.83 (br s, 2H), 2.88 (br s, 2H), 1.51 (s, 9H).

Workup

  1. customPurification by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2c27be64ca154787a5f8ba1568ccc678
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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