4-Toluenesulfonyl chloride → 5-benzylhexahydro-1H-furo[3,4-c]pyrrole

HRID 1283606Notes

Reaction equation

HRID 1283606 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[S:12]([O:22][CH2:23][CH:24]1[CH:28]([CH2:29][O:30][S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:27][O:26][CH2:25]1)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[CH2:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:41]([N:48]1[CH2:23][CH:24]2[CH2:25][O:26][CH2:27][CH:28]2[CH2:29]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[S:12]([O:22][CH2:23][C@H:24]1[C@@H:28]([CH2:29][O:30][S:31]([C:34]2[CH:35]=[CH:36][C:37]([CH3:38])=[CH:39][CH:40]=2)(=[O:33])=[O:32])[CH2:27][O:26][CH2:25]1)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7504BenzylamineHCID 215185433,4-Bis(tosyloxymethyl)tetrahydrofuran2×

Product 2

HCID 215185425-benzylhexahydro-1H-furo[3,4-c]pyrroleHCID 53856916cis 3,4-Bis(tosyloxymethyl)tetrahydrofuran

Procedure

Using another route as shown in the accompanying schematic, one mole of the mixture of the cis-trans 3,4-bis (hydroxymethyl)tetrahydrofuran (III) can be reacted with p-toluenesulfonyl chloride according to the process of Example 9 to form a cis-trans mixture of 3,4-bis(tosyloxymethyl)tetrahydrofuran (XIX). This product, (XIX), can in turn be reacted with benzylamine according to the process of Example 10 to form 5-benzyl hexahydro-1H-furo(3,4-c)pyrrole (IX) from the cis 3,4-bis(tosyloxymethyl)tetrahydrofuran. 5-Benzyl hexahydro-1H-furo( 3,4-c)pyrrole (IX) is separated from the reaction product mixture by distillation at about 95° to 105°C. at 0.15 mm Hg. This product in turn can be debenzylated according to the method of Example 11 to form hexahydro-1H-furo(3,4-c)pyrrole.

Workup

  1. customto form

Sources & evidence

ORD record
ord-657fc91dc5b445b48e2cb234a31f8a1d
Source dataset
uspto-grants-1976_08
Patent number
US03975532

Reaction notes

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