Triphenylphosphine → HCID 68962618, compound

HRID 2116112Notes

Reaction equation

CC1C=CC(S(OCC2CC3C=C(Cl)C=C(C(C)(C)C)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:31]([CH2:34][CH:35]1[CH2:39][C:38]2[CH:40]=[C:41]([Cl:48])[CH:42]=[C:43]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:37]=2[O:36]1)=[N+]=[N-].[N-]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:44]([C:43]1[C:37]2[O:36][CH:35]([CH2:34][NH2:31])[CH2:39][C:38]=2[CH:40]=[C:41]([Cl:48])[CH:42]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

Reactant 5

HCID 11776Triphenylphosphine

HCID 33557Sodium Azide

HCID 33558Azide

HCID 86599072HCID 86599072, compound

HCID 86599185HCID 86599185, compound

Product 1

HCID 68962618HCID 68962618, compound

Procedure

Treatment of (±)-(7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (13.74 g, 34.8 mmol) with sodium azide (9.05 g, 0.139 mol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran. Treatment of the azide with triphenylphoshine (9.13 g, 34.8 mmol) generally according to the procedure described for Example 21 afforded 4.43 (46 of (±)-1-(7-tert-butyl-5-chloro-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 229-231° C.; Anal. calcd. for C13H18ClNOHCl: C, 56.53; H, 6.93; N, 5.07. Found: C, 56.49; H, 6.71; N, 4.86.

Sources & evidence

ORD record: ord-ec2a6c0992034556bcfc80582bbd291b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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