4-Nitro-1-naphthol → tert-Butyl (3S)-3-[(4-nitro-1-naphthyl)oxy]pyrrolidine-1-carboxylate

HRID 549276

Reaction equation

HRID 549276 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[N+:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](O)=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[N+:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([O:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 3438294-Nitro-1-naphtholHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 67156935tert-Butyl (3S)-3-[(4-nitro-1-naphthyl)oxy]pyrrolidine-1-carboxylateYield 88%

Procedure

The compound was prepared from tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate (3.56 g, 19 mmol) and 4-nitro-1-naphthol (3 g, 15.9 mmol). Yield: 5 g (88%) of the title compound as yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.45 (d, J=7.03 Hz, 9H) 2.22-2.38 (m, 2H) 3.54-3.83 (m, 4H) 5.18 (br s, 1H) 6.74 (d, J=8.53 Hz, 1H) 7.56 (t, J=7.78 Hz, 1H) 7.71 (t, J=7.78 Hz, 1H) 8.29 (d, J=8.53 Hz, 1H) 8.33 (d, J=8.53 Hz, 1H) 8.72 (d, J=8.53 Hz, 1H). MS (ESI+) for C19H22N2O5 m/z 376.2 (M+NH4)+, 303.2 (M−tBu)+. HPLC 100%, RT=2.768 min (System A1, 10-97% MeCN over 3 min).

Sources & evidence

ORD record
ord-92608fada2164eb7a0d32b8dbf9efa5e
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Linked notes

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