Diisopropylethylamine → 1009368-28-8

HRID 1051163Notes

Reaction equation

HRID 1051163 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.CCN(C(C)C)C(C)C.[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Cl:22][C:23]([O:1][CH:2]1[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]1)=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 576866831009368-28-8Yield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-hydroxy-1-Boc azetidine (21; 350 mg, 2.023 mmol) and DIPEA (1.3 ml, 7.080 mmol) in THF (5 ml) at 0° C. was slowly added triphosgene (898 mg, 3.034 mmol). The resulting mixture was stirred for 2 hr at RT. After completion of the reaction, the reaction mixture was filtered and washed with fresh THF to get rid of inorganic salts. The filtrate was concentrated under reduced pressure to get crude product 61 in 55% yield. The crude product, thus obtained, was immediately used for the next reaction.

Workup

  1. customat 0° C.
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. washwashed with fresh THF
  5. customto get rid of inorganic salts
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto get crude product 61 in 55% yield

Sources & evidence

ORD record
ord-f0f4ee96e03d4824a54279b02f13644e
Source dataset
uspto-grants-2016_07
Patent number
US09388164B2

Reaction notes

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