1,2-Dichloroethane → HCID 69516023, compound

HRID 1297225Notes

Reaction equation

HRID 1297225 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:17]([OH:19])=O)[C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:26]C=2C=1.CN1CCOCC1.C(Cl)CCl.[OH-].[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1([C:17](=[O:19])[NH2:26])[C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 69515820HCID 69515820, compound

Product 1

HCID 69516023HCID 69516023, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylaminomethyl)-spiro[2.4]heptane-1-carboxylic acid (12.5 g, 46.6 mmol) in THF (450 mL) was added HOBT (6.6 g, 48.9 mmol), 4-methylmorpholine (5.4 mL, 48.9 mmol) and EDC (9.83 g, 51.3 mmol). The reaction mixtured was stirred for 3 hours and then concentrated aqueous ammonium hydroxide (6.3 mL, 93.2 mmol) was added. The reaction mixture was stirred for 48 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (500 mL) and half saturated potassium hydrogen sulfate solution. The layers were separated. The organic layer was washed with half saturated potassium hydrogen sulfate, saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated to give 9.7 g (78%) of (1-carbamoyl-spiro[2.4]hept-1-ylmethyl)-carbamic acid tert-butyl ester as a white solid: 1H NMR (300 MHz, CDCl3) δ 0.74 (d, J=4.5 Hz, 1H), 1.38 (d, J=4.5 Hz, 1H), 1.44 (s, 9H), 1.6-1.8 (m, 7H), 1.83 (m, 1H), 3.15 (dd, J=5.1, 14.8 Hz, 1H), 3.65 (dd, J=5.1, 14.8 Hz, 1H), 5.0 (br s, 1H), 5.49 (br s, 1H), 6.45 (br s, 1H); MS (APCI) m/z 169 [M+H-100(Boc)]+.

Workup

  1. customThe reaction
  2. stirringThe reaction mixture was stirred for 48 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (500 mL) and half saturated potassium hydrogen sulfate solution
  5. customThe layers were separated
  6. washThe organic layer was washed with half saturated potassium hydrogen sulfate, saturated sodium bicarbonate, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-93f1c9f9d9204bfc838af665d042f776
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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