Hydrochloric Acid → tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

HRID 549330Notes

Reaction equation

HRID 549330 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:16])[N:19]([O:20][CH3:21])[CH3:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acid

Product 1

HCID 21988510tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (RS)-1-(tert-butyloxycarbonyl)-2-piperidine carboxylic acid (5.32 g, 23.2 mmol) in dichloromethane (20 ml) was added sequentially N,O-dimethyl hydroxylamine hydrochloride (2.68 g, 27.5 mmol), triethylamine (12 ml, 86.0 mmol) and py-BOP (13.2 g, 25.4 mmol). The resultant mixture was stirred at ambient temperature for 6 h, then diluted with dichloromethane (350 ml) and poured into 1M HCl (50 ml).

Sources & evidence

ORD record
ord-5fed1c9832e1419cb2871d8b42ebd8e2
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

Loading…