1,4-Dioxa-8-azaspiro(4.5)decane → 1,4-Dioxa-8-azaspiro[4.5]decane-8-carboxamide

HRID 2100419Notes

Reaction equation

HRID 2100419 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C[Si]([N:15]=[C:16]=[O:17])(C)C>C(O)(C)C>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:16]([NH2:15])=[O:17])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 70696Trimethylsilyl isocyanate

Product 1

HCID 573210241,4-Dioxa-8-azaspiro[4.5]decane-8-carboxamideYield 102.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 1,4-dioxa-8-azaspiro[4,5]-decane (1.1 g, 7.67 mmol) in isopropanol (20 mL) at rt was added trimethylsilylisocyanate (1.5 mL, 10.6 mmol) and the resulting solution stirred overnight before the volatiles were removed in vacuo to give 1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid amide (1.47 g, quant.); 1H-NMR (300 MHz, d6-DMSO) 5.96 (2H, s), 3.88 (4H, s), 3.33 (4H, t), 1.51 (4H, t).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-74a499333dcf48b68833306d42f13781
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

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