Ammonia → Dibenzyl 2-methylazetidine-1,2-dicarboxylate

HRID 1987515Notes

Reaction equation

HRID 1987515 reaction equation
[N:1]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:4][CH2:3][CH:2]1[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].IC.[CH3:27][Si]([N-][Si](C)(C)C)(C)C.[Na+].N>C1COCC1>[CH3:27][C:2]1([C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])[CH2:3][CH2:4][N:1]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 14683726Dibenzyl azetidine-1,2-dicarboxylate

Product 1

HCID 66751005Dibenzyl 2-methylazetidine-1,2-dicarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of Example 22A (325 mg, 1 mmol) and iodomethane (0.12 ml, 2.0 mmol) in THF (5 mL) was treated with NaN(TMS)2 in THF (1.0 M, 2 mL, 2.0 mmol) at −70° C. under nitrogen. The temperature of the cooling bath was slowly raised to −20° C. within 1 h and the mixture was stirred at the same temperature for additional 2 h. After quenching with water, the mixture was partitioned between water and EtOAc. The organic phase was washed with water and concentrated. The residue was purified on flash column chromatograph to give Example 22B. (250 mg, 77% yield). MS (DCI/NH3) m/z 340 (M+H)+.

Workup

  1. customAfter quenching with water
  2. customthe mixture was partitioned between water and EtOAc
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customThe residue was purified on flash column chromatograph
  6. customto give Example 22B

Sources & evidence

ORD record
ord-65cbd183a9ca48a692b38bdafee78d0f
Source dataset
uspto-grants-2009_06
Patent number
US07550603B2

Reaction notes

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