Diisopropylethylamine → HCID 59606087, compound

HRID 1922720Notes

Reaction equation

HRID 1922720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][NH:13][CH2:14]C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:16]1[CH2:20][CH2:19][C:18](=O)[CH2:17]1.C(N(C(C)C)CC)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][N:13]([CH3:14])[CH:18]2[CH2:19][CH2:20][O:16][CH2:17]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5293923-OxotetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 53415261HCID 53415261, compound

Product 1

HCID 59606087HCID 59606087, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-ethylaminomethyl-azetidine-1-carboxylic acid tert-butyl ester (200 mg, 1.0 mmol), dihydrofuran-3-one (0.155 mL, 2.0 mmol), diisopropylethylamine (0.347 mL, 2.0 mmol) and 4 Å molecular sieves (600 mg) in DCM (10 mL) was stirred at RT for 30 min. Sodium triacetoxyborohydride (424 mg, 2 mmol) was added and the resulting reaction mixture was stirred at RT under nitrogen atmosphere for 60 h. The suspension was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95) to afford the title compound as a colourless oil (257 mg, 95%). 1H NMR (400 MHz, CDCl3): δ 4.04-3.92 (3H, m), 3.83 (1H, dd, J=8.89, 6.90 Hz), 3.75 (1H, q, J=8.07 Hz), 3.64 (1H, dd, J=8.87, 6.21 Hz), 3.56-3.55 (2H, m), 3.14 (1H, m), 2.67-2.66 (2H, m), 2.51 (1H, dd, J=12.33, 7.20 Hz), 2.17 (3H, s), 2.05 (1H, s), 1.89-1.79 (1H, m), 1.44 (9H, s).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at RT under nitrogen atmosphere for 60 h
  3. filtrationThe suspension was filtered through Celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95)

Sources & evidence

ORD record
ord-d6205e9853cd418fbc6970ba54b70bed
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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