Sodium Azide → HCID 68961528, compound

HRID 2116111Notes

Reaction equation

HRID 2116111 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C(C)(C)C)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:30]([CH2:33][CH:34]1[CH2:38][C:37]2[CH:39]=[CH:40][CH:41]=[C:42]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:36]=2[O:35]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[C:43]([C:42]1[C:36]2[O:35][CH:34]([CH2:33][NH2:30])[CH2:38][C:37]=2[CH:39]=[CH:40][CH:41]=1)([CH3:46])([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599070HCID 86599070, compoundHCID 86599184HCID 86599184, compound

Product 1

HCID 68961528HCID 68961528, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(7-tert-butyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (12.43 g, 0.035 mol) with sodium azide (6.73 g, 0.103 mol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-tert-butyl-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.750 g, 10 wt. %) generally according to the procedure described for Example 1 gave 5.56 g (67%) of (±)-1-(7-tert-butyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 177-180° C. (dec); Anal. Calcd. for C13H19NOHCl: C, 64.59; H, 8.34; N, 5.79. Found: C, 64.34; H, 9.19; N, 5.73.

Sources & evidence

ORD record
ord-74e6f372b96f449a8fb26c30352904b5
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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