(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → 3-(1-Aminoethyl)-1-(4-chloro-5-isoquinolinesulfonyl)azetidine

HRID 2425430Notes

Reaction equation

HRID 2425430 reaction equation
BrC1C2C(S(Cl)(=O)=O)=CC=CC=2C=NC=1.C(OC(N[C@H]1CCNC1)=O)(C)(C)C.C(OC([NH:36][CH:37]([CH:39]1[CH2:42][N:41]([S:43]([C:46]2[C:47]3[C:48]([Cl:56])=[CH:49][N:50]=[CH:51][C:52]=3[CH:53]=[CH:54][CH:55]=2)(=[O:45])=[O:44])[CH2:40]1)[CH3:38])=O)(C)(C)C>>[NH2:36][CH:37]([CH:39]1[CH2:40][N:41]([S:43]([C:46]2[C:47]3[C:48]([Cl:56])=[CH:49][N:50]=[CH:51][C:52]=3[CH:53]=[CH:54][CH:55]=2)(=[O:44])=[O:45])[CH2:42]1)[CH3:38]

Participants

4

Reactant 3

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 145800584-Bromo-5-isoquinolinesulfonyl chlorideHCID 672444683-[1-(Tert-butoxycarbonylamino)ethyl]-1-(4-chloro-5-isoquinolinesulfonyl)azetidine

Product 1

HCID 672441893-(1-Aminoethyl)-1-(4-chloro-5-isoquinolinesulfonyl)azetidine

Procedure

4-Chloro-5-isoquinolinesulfonyl chloride obtained in Reference Example 7 and 3-[1-(tert-butoxycarbonylamino)ethyl]azetidine obtainable from 1-(diphenylmethyl)-3-(hydroxymethyl)azetidine (Oakwood) according to the method described in WO05/080394 can be used in the method of Example 1-1, Step A instead of 4-bromo-5-isoquinolinesulfonyl chloride and (S)-3-(tert-butoxycarbonylamino)pyrrolidine, respectively, to prepare 3-[1-(tert-butoxycarbonylamino)ethyl]-1-(4-chloro-5-isoquinolinesulfonyl)azetidine, and the protective group of the obtained compound can be removed according to the method described in Example 1-1, Step B to obtain the title compound.

Workup

  1. customthe protective group of the obtained compound can be removed

Sources & evidence

ORD record
ord-f391dcb2f3ea4081b9ce02040852312f
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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